Interview With Garry Tan: “Never Fear Failure”

The HelloSign Speaker Series invites experts in tech fields to visit the HelloSign HQ. Garry Tan – partner at Y combinator and one of the original employees at Palantir (he designed the Palantir logo!) – recently stopped by the HelloSign office to talk Silicon Valley and share his experience working in and with startups.

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Garry Tan: Designer. Engineer. YC Advisor. Unicorn.

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A designer, investor, and engineer, Garry Tan is what’s known as an industry “unicorn” in the tech world. But beyond the well-earned mythical status (he exists – we can confirm this!), Garry maintains the humility and perspective of a great mentor.

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As Hellosign’s CEO Joseph Walla puts it, “Garry represents Silicon Valley at its very best.”
Here’s what Garry had to say about coaching startups, what founders can do to bring their company to the next level, and the question that all startups should be asking.

1. Lessons learned from Posterous: “What got you here won't get you where you want to go.”

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“At my last startup [Posterous] we were growing 30 - 50% every month for about 2.5 years and we even got to be a top 500 website.

It was an incredible achievement, but we kept doing what got us to that point: keeping it free and trying to keep releasing new features. Ultimately, that prevented us from focusing on other key issues that were asking to be solved. If I could do it again, I’d approach it a different way today: 1. Charge money and 2. Get infinite runway so I could keep experimenting to figure out the growth.

In our case rather than continuing to focus on features, we needed to make the site fast again for our most important users, the content creators.”

2. Garry’s biggest success: “YC is probably the craziest thing I get to work on on a daily basis.”

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“YC is turning into a university of sorts. That’s totally different from when I started and there were just 3 or 4 people. To watch that evolution is exciting.

When I was first there it boggled my mind; it didn’t make sense to me that so many great companies and founders could come together. Now, I realize that there are a lot of incredible people out there. There are entire communities out there who are dedicated to opening that creative and innovative space up.”

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3. What gets a startup to the next level: “Make performance a priority.”

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“As mentioned, most companies reach a point that what got them there might not get them to the next point.

One thing that does kill a product is if it’s slow or even if it’s slow enough. It doesn’t even have to be super slow, it can just be a little slow and people will stop using it. If it becomes painful enough to use that people think twice – that’s all that it takes to make a graph flatline.”

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4. Scaling company culture: “A lot of it comes down to hiring.”

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“Be vigilant in asking, ‘Are they talented? Are they a good person?’ Be good to each other. But a lot of it starts with hiring.”

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5. Startup trends that might warrant a gut check: “Software created only for people in San Francisco.”

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“On the one hand – yes, convenience is good. But on the other hand, I think there’re a lot of startups that can only be useful for engineers in the Silicon Valley.

It’s understandable why that’s happening. But I worry sometimes that the valley is getting too focused on these marginal things. I want to work with and invest in teams that are working on something foundational – the ones that could affect a billion people instead of 30,000 Google engineers.”

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6. The one question that startups typically don’t ask, but should: “Where am I failing?”

“A new trope at YC – we realize now – is that the companies that ask us if they’re failing are the ones who never fail. If you ask us that question, then that’s pretty good. So you should ask us that.

In abstraction, it makes sense why that’s true. If you don’t take a moment to consider whether failure is a thing you can be in, you might never realize it. Some startups are just ticking off the checkboxes, but that doesn't mean these checkpoints are translating into a successful business.”